A new documentary explores Playboy founder Hugh Hefner’s impact not just on sexual mores but on civil liberties and life as we know it

In 1953, 27-year-old Hugh M. Hefner set out to change America’s relationship with sex. Working from the kitchen of his Chicago apartment, with a $1,000 loan from his mom, the former Esquire copywriter created a magazine whose pictures of nude young women and feature articles by big-name writers forever altered how we define allure. It can be easy to dismiss Hefner, now 84, as a caricature (the robe! the pipe! the Bunnies!), but a new documentary in theaters July 30 offers a more serious take. Hugh Hefner: Playboy, Activist and Rebel reveals his lifelong commitment to preserving civil rights and freedom of expression. Filmmaker Brigitte Berman, who won an Oscar for her 1985 documentary, Artie Shaw: Time Is All You’ve Got, portrays Hef as an outspoken foe of segregation and censorship and an early advocate for gay and lesbian rights and legal access to abortion and contraception. So what if he has several girlfriends at any given time. Revolutionaries, Berman’s film shows, are a complex breed. We sat down with the ever frisky yet genteel Hefner in the wood-paneled library of the Playboy Mansion in Holmby Hills to talk about morality, his efforts to save the Hollywood sign, and the downside of Viagra.

Some people see you as anti-woman. Does that bother you?Yes, it does trouble me, but I also understand it. America is very hung up on sex. The Puritans left England to escape religious persecution and promptly turned around and started persecuting the other people they didn’t agree with here in America, and most of it had to do with sex. Because of the nature of my life, it’s difficult for people to recognize that a person can live a full life, and maybe an unorthodox life, and still be on the side of the angels. The very notion, on any level, that I’m anti-woman is a reflection of the people who are projecting these views. It’s a Rorschach test. The very nature of my life and the nature of Playboy are inkblot tests. They’re a mirror of people’s own dreams, fantasies, and prejudices.

Is that still true?Sure. These are particularly curious times because Playboy has managed to play a major role in changing sexual attitudes and, in a certain sense, behavior. When I started Playboy, nice middle-class young people couldn’t live together. Literally. It was a different world, and Playboy played a part in changing that. When I started the magazine, models in the women’s magazines looked more mature. Even young women wore girdles, pointy bras, skirts down to there. I didn’t like any of that. With Playboy, dressed or undressed, I went with a much more natural look—what came to be called the “girl next door.” The suggestion was that beauty is everywhere.

You were under FBI surveillance for a time. What were they looking for? I think a lot of people recognized, certainly in the ’60s, that the FBI had a political agenda that wasn’t just crime fighting. John Lennon was on the list. Martin Luther King Jr. was on the list. It was a very strange time, and Hoover was a strange man. He literally had an agent in the early ’60s assigned to read every page of the magazine. It was a great assignment!

That’s hilarious. Yes, but it is black comedy. I think that what actually caught Hoover’s interest was less the girls, quite frankly, than the fact that we made a couple of references to the FBI in less than flattering ways because they were doing things they shouldn’t have been doing.

So what were they looking for? Who knows? There were secret files of so many celebrities. For Hoover, I think it was a sense of power. I think if he had not managed to collect a great deal of secret information on people in politics, he would not have continued in that position for all those years. Presidents came and went, but Hoover continued because he had the goods on them.

When you launched Playboy, the man you were speaking to was a Don Draper type. Do you watch Mad Men? Yes, sure. The show has a Playboy sensibility. I don’t think there’s any doubt about that. The best of Mad Men is a parody. When you see pop culture from a little distance, one can see the humor and the irony.

That sensibility is so much a part of the cultural fabric now that people forget there was a time before it existed. It’s true. When I started Playboy, the Bunnies were controversial. When we were gonna open a club in Boston, one of the liquor commissioners turned around in his chair and refused to look at the Bunny in her costume. In New York you needed two licenses—a liquor license and a license for entertainment. And we didn’t get the entertainment license for about a year because the head of the license bureau was a good Catholic who had studied for the priesthood and didn’t think the Bunnies were very nice. When he was replaced by a good Jewish guy who didn’t let his religion get in the way of his politics, then we got that one.

You had a special subscription rate for members of the clergy. Did priests actually take you up on that? Yes! Playboy caused a tremendous stir. It came at a time when society was ready to change. The same questions were being raised on the liberal side of organized religion. So there was a lot of debate.

In the documentary you flatly reject the idea that Playboy is porn. I’ve never considered Playboy porn. If pinup pictures are pornography, then we’ve lost our use of language. The pictures in Playboy are direct descendants of the pinup pictures during World War II—the calendar pictures that I grew up with as a kid. Porn is simply a negative label for things erotic. If you don’t like it, you call it porn. “Pornography” refers specifically to hard-core, explicit sex. When you say “hard-core pornography,” then you start saying “soft-core porn,” and what does that mean—something that in any way has any kind of sexuality to it? The crazy part for me is the notion that obscenity itself should be linked to sex instead of the things that are really obscene. Aren’t the obscene things on the planet really war, bigotry, famine, overpopulation? It’s another example of how screwed up we are in terms of our sexuality. Sex is not the enemy.

Come on. You’ve got to admit that today’s Playboy Playmates have a really porny look. Well, you must be lookin’ at some very good porn! The Playmates intentionally are clean and healthy and all-American—that’s the whole girl-next-door notion.

But there’s been an evolution in the Playboy aesthetic. Where once the women were full figured and voluptuous, now they’re streamlined and spray tanned and hairless. Are you gonna blame me because the girls all went hairless? [Laughs.] We reflect the changing pop culture values. I think that’s probably where a great many people suddenly discovered that you women had removed your pubic hair. It was in the pages of Playboy, and where did that suddenly come from?

Where did it come from? I have no idea.

But don’t you think it came from porn? No, I don’t. Maybe there was some lack of pubic hair in some porn that had some influence. But I doubt it, because it’s the women who make the decision, and I don’t know if women were watching a lot of porn, so that doesn’t really make sense. The disappearance of pubic hair was not motivated by men.

And when did that happen? I don’t know. I can tell you when the miniskirt arrived, but I can’t tell you when pubic hair disappeared.

When Playboy got started, sexual imagery was inaccessible and illicit. Now it’s accessible to everyone. How does that sit with you?I think there should be an adult society and that young people should grow up in a protected, innocent kind of world. And that, of course, is very difficult with the Internet. I think it skews us. Technology has changed things in a lot of ways. When I was growing up, there were a few people on the stage, so to speak, in the movies or recording artists, and the rest was an audience. Today everybody wants to be on the stage. Wearing skirts up to their eyeballs, shaking their booties. The fact that girls grow up too fast and dress like sluts—I think it’s sad.

You moved to L.A. from Chicago in 1975, yes? I got this house in ’71. And I was moving back and forth between here and Chicago, and in ’75 I finally stopped going back and stayed.

Why? My dreams came from here. From the movies. I grew up spiritually in two cities from the very beginning. Chicago was my roots, and Hollywood was the place of my dreams. One of the things that is unique about Hollywood is that young, attractive people came here to get into the movies. If they didn’t make it, they stayed, and they wound up getting married and having beautiful children. So you have a more attractive population per capita than anywhere else in the world.

Is that part of the reason you recently donated $900,000 to save the Hollywood sign?Yes. It’s a way of paying back what the movies and Hollywood gave me. I’ve also given several million dollars to UCLA and USC for film classes, film preservation, documentaries devoted to early Hollywood. The movies are the best export that America has ever produced. When they talk about the American dream, that doesn’t come from Washington. It comes from movies by Capra and Ford. Immigrant dreams.

There has long been talk of a major motion picture being made by producer Brian Grazer about your life. You tweeted recently that you were meeting with Juno writer Diablo Cody to discuss the project. Where does that stand? I’m waiting for a screenplay.

When do you expect it? I don’t know, but I said to Brian not long ago, “I’d like it to not be a posthumous tribute!”

You’re a big tweeter.Yes! [Laughs.] Crystal, my girlfriend, gave me an iPad for my birthday. I’ve gotten competent. I can do it myself.

So you used to have someone tweet for you?Until I learned how, yeah.

From your Twitter feed, it seems like your life is one continuous rotation of backgammon games, movie nights, and cuddle sessions. Is that accurate?Yeah, it’s the best life in the world! On more than one occasion I have been asked, “Is your life as good as it seems?” The honest answer is, “It’s better.” Anybody is lucky who dreams impossible dreams and makes them come true. I take tremendous pride in the impact I have had on society, but to do that and also be in a loving relationship surrounded by loving friends [has been amazing]. If you’re a celebrity, life usually has a peak and a valley. It hasn’t been like that for me. There was a point in the ’80s and ’90s when it was a valley, but now it’s back up there again, and I’m in my eighties!

Did you anticipate that comeback?Perhaps I should have, but I didn’t. It’s directly connected to the fact that when I got married [to Kimberley Conrad] in 1988, it was as if I had died. I was off the scene for about eight or ten years. So when the marriage ended in 1998, it was like Elvis Presley had suddenly shown up at a supermarket. He wasn’t dead. The party started again. All the celebrities who had grown up on the mystique of Playboy came crowding back to the Mansion, and it just became an incredible phenomenon all over again, and it hasn’t ended since. Then of course we started The Girls Next Door, and that became a global phenomenon, with more female followers than male.

Speaking of female followers, how do you have multiple girlfriends at once? Isn’t that a lot to handle?Depends on who the girls are. Before Holly, Bridget, and Kendra, at one point I had seven girlfriends all living here. That was pretty messy because they were pretty competitive. I came out of my marriage a little beat up and emotionally bruised. I had been faithful, and she was the one who decided to leave. So I think that the multiple dating was overcompensation. I met Brande Roderick very soon after that breakup. And then the Bentley twins almost at the same time. And it just sort of happened. So I was with the three of them for about two years, and that was the beginning of that pattern.

How does it work logistically? Is it like Big Love, where you spend a night with each woman? No, it’s like “Big, Big Love,” with all of them together.

Every night? No. There is always a primary relationship. With Holly, Bridget, and Kendra, Holly became the primary relationship, and then became more important, so by the tail end of the relationship, all three of them were living here, but the romantic relationship essentially was Holly. It may seem unorthodox, but the reality is, it was very typical. You just multiply it, that’s all. Quite frankly, it is more moral because there isn’t any slippin’ around. In typical relationships, married or single, there’s a lot of cheating. And I don’t like cheating.

Is it difficult to grow older? It is my experience that age is almost meaningless. I’m no different now than I was—I’m just more interesting. It’s a little unfair now to make that comparison, because you reach a certain status that has kind of an iconic quality. I get several letters a week from girls I don’t know, in their late teens or early twenties, who would like to be my girlfriend—much more so now than when I was 20 or 30 years old. If a person is a fan of Mick Jagger, they don’t care how old he is. It’s their only chance to be with Jagger. Well, that’s the way it is with me.

Don’t you worry that they’re more interested in the icon than the man? But isn’t that me? [Laughs.] What do you think that is? You think that’s something someone else invented?

Do you buy Viagra in bulk? Where do you keep it? In the medicine chest! One has to be concerned in terms of how much you take. I have lost some of my hearing, and I think that’s because of Viagra. It can have an impact on hearing and eyesight.

You helped usher in an era of sexual liberation, allowing for many of the forces—particularly Internet porn—that some believe now make Playboy irrelevant. How can it compete? I think the real question is, Are magazines relevant? Is there more to compete with? Yes, absolutely, but that isn’t unique to Playboy. Because Playboy never has sold itself primarily on sex. It’s a lifestyle magazine. It was the combination of the lifestyle and the sexuality.

Playboy had net losses last year. People are saying this is the end of the empire. Is it? [Laughs.] This has been a very difficult time economically, without question, but the brand is hotter now than probably ever.

How many times throughout your career have you heard “This is it—it’s over for Playboy”? More than a few. Newsweek did a cover story about me in the late ’80s that was called “The Party’s Over.”

And now Newsweek is on the block. Do you ever think you’ll hang up your robe? Remaining involved in all of this is what keeps me alive. I feel younger now in my eighties than I did 20 years ago, and it’s because I stay active. If you’re doing what you really believe in, you get great satisfaction.

How do you think you’ll be remembered? As someone who played some significant part in the changing social-sexual values of his time. And I’m pretty secure in that. That was a home run.

Hef’s Female Boswell

Oscar-winning filmmaker Brigitte Berman on Playboy‘s creator

You went from making a film about Artie Shaw to this one about Hugh Hefner–you really cover the waterfront.

Actually, I made a film in between about the murder of a Jesuit priest! I’m always drawn to complex individuals who have had lives full of conflicts that matter. My very first feature documentary was on Bix Beiderbecke, the jazz musician. Several years after it was made, Hef discovered it. His assistant called and asked me to send a copy. She said, “I’m calling from the Playboy Mansion.” Of course I hear that and I think, “Sure, tell me another one.”

What was your first meeting like? I always thought he was a playboy and womanizer—and then we started talking about music and film, and I was so struck by how different he was from what I had imagined. He came across as a charming, thoughtful, smart man who happened to wear pajamas.

Did you have to talk Hef into letting you do the documentary? When I sent the treatment, the next day I received a fax from him saying, “I love it, whenever you want to start, anything you need.” He knew I would tell a fair story. He has made over 2,000 scrapbooks about his life—I went through just about all of them. I had total, unprecedented access and creative freedom. It was an incredible gift but a responsibility, too, and I also didn’t want to whitewash him. It was very important to me that the naysayers and the yea-sayers were there.

So what was your biggest insight? When I started the film, I called it The Para-dox of Hugh Hefner. By the time I finished researching, “paradox” was no longer the right word. He is an individual of many, many facets who dared to do many, many things. Thus the film’s title, Hugh Hefner: Playboy, Activist and Rebel.